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3.2 Ecofriendly Sample Preparation Techniques 49
Analytes Matrix Sample volume
Elution solvent
volume References
Cocaine and metabolites Hair
samples
0.15 mL 100 μL 2%
ammonium
hydroxide in MeOH
[70]
Δ9-tetrahydrocannabinol
(THC)
and metabolites
Urine
samples
0.30 mL 100 μL 90% AcN [71]
AcN, acetonitrile; DCM, dichloromethane; H
2
O, water; IPA, isopropanol ammonium hydroxide; MeOH,
methanol; NH
4
OH, ammonium hydroxide.
Table 3.4 (Continued)
This procedure has been employed for different compounds and in numerous matrices
(food, cosmetic, biological, etc.). For example, this technique was successfully applied for
the determination of hormones in environmental and biological samples [72, 73]; benzodi-
azepines (bromazepam, diazepam, lorazepam, and alprazolam) in blood serum [74]; azole
antimicrobial drugs in biological fluids [75]; aromatase inhibitors in whole blood, plasma,
and urine [76]; endocrine-disrupting chemicals (EDCs) in various biological fluids [77–81];
antidepressant drugs in urine [82] and other biological fluids [83]; antibiotic residues [84,
85] in food and biological samples; non-steroidal anti-inflammatory drugs (NSAIDs) in
saliva samples [86]; β-blocker drugs from human serum and urine [87]; and phenolic com-
pounds in human saliva samples [88].
Locatelli and co-workers [89] presented an advanced application of FPSE as an in vivo sam-
pler for the evaluation of exhaled breath aerosol (EBA). In this work, an array of six mem-
branes (fabric phase sorptive membrane, FPSM) possessing different characteristics (non-polar,
medium-polar, and polar) was built. The FPSM array was then inserted inside the facemask
and 15 volunteers were involved for the sampling. Once removed, a mixture of MeOH and AcN
(150 µL) was used for the elution of extracted compounds. The samples were then analysed
using LC tandem mass spectrometry through rapid screening that permitted the rapid qualita-
tive analysis of more than 700 compounds. This study undoubtedly represents a potential
implementation of biomonitoring of different compounds and its applicability could also be
extended to other fields. Moreover, particular attention was paid to the sustainable profile of
the method, also evaluated through the green analytical procedure index (GAPI) [90]. The
GAPI allows, following the indicated parameters, critical evaluation of the specific compo-
nents of the analytical procedure (solvents, energy consumption, volumes of discharge, etc.);
everything is shown in a pictogram that gives a visual idea of how green the proposed appara-
tus or practice is. The evaluation carried out in this study showed a fairly good green profile.
FPSE represents a novel sample preparation technique that offers numerous benefits such as
ease of application, superior performance, and broad applicability due to the availability of
numerous adsorbents. This technique certainly reflects the principles of GAC, such as the
reduced consumption of organic solvents, the possibility of analysing a complex matrix without
pre-treatment steps, sample volume reduction, and the opportunity to carry out less invasive
sampling. All these advantages are accompanied by excellent analytical parameters, as demon-
strated by the good performance in terms of accuracy and precision in the validated methods.
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3 Modern Green Extraction Techniques50
3.3 Solvent-Based Microextraction Procedures
3.3.1 Liquid Phase Microextraction
LLE is a technique that involves the partitioning of analytes from an aqueous phase to a
water-immiscible solvent based on solubility. It was definitely one of the first separation
techniques developed and is among the most generally used. Recently, the diffusion of SPE
techniques and the subsequent miniaturisation have certainly made LLE less widespread.
The time requirement, the low extraction efficiency, the high chemical and solvent con-
sumption, and the high cost are some of its disadvantages. Miniaturisation has been a key
element to overcome some of these limitations, and as a result liquid phase microextraction
(LPME) was launched in the 1990s [91]. LPME uses a few microlitres of a water-immiscible
solvent extraction phase and an aqueous sample phase, which contains the selected ana-
lytes [92]. Dispersive liquid-liquid microextraction (DLLME), which immediately attracted
scientist attention, involves the rapid addition of a dual system of solvents (extraction sol-
vent and dispersant solvent) that leads to the formation of a turbid mixture in which the
extraction solvent is spread within a type of small droplets. Extraction equilibrium is
reached quickly, thanks to the wide contact area between the droplets and the sample, and
the analytes are extracted. The mixture is thus centrifuged to collect the organic solvent in
the lower or upper part (depending on the density of the extraction solvent) and the trans-
ferred phase is collected for instrumental analysis. Another improvement in DLLME was
the application of ionic liquids (ILs) as alternative solvents. This technique, named
IL-DLLME, avoiding the use of toxic solvents, is considered environmentally sustainable.
ILs are considered further in the next section.
3.3.2 Ionic Liquids and Deep Eutectic Solvents
The search for more sustainable solvents and reagents has become the new challenge of the
entire analytical procedure. In this context, new solvents have been proposed that contrib-
ute to greening analytical practices.
ILs are composed entirely of ions and include numerous compounds with particular
characteristics such as minimal volatility, miscibility with both water and organic solvents,
elevated thermal stability, and the absence of inflammability. They are identified as ‘design
solvents’ as it is possible to vary the physical and chemical properties to replace the compo-
nents and make them more suitable to meet the requirements [93]. ILs are considered eco-
friendly solvents because they do not discharge toxic vapours into the surrounding
environment. In contrast, the process of synthesising ILs often involves steps that limit
their green characteristics; therefore, this designation is rather controversial. Research in
this area is gradually moving towards further recyclable and fewer lethal preparations and
advanced techniques, such as microwave irradiation and eco-assisted reactions, which
have significantly expanded the environmental impact of IL synthesis in addition to leading
to higher reaction yields. ILs have been successfully applied in different fields of analytical
chemistry, like chromatography, CE, mass spectrometry, and extraction and (micro)extrac-
tion techniques, as a substitute for conventional reagents. In Table 3.5 some recent applica-
tions and techniques that involve the use of ILs are reported.
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Table 3.5 Recent applications of ionic liquids (ILs) and deep eutectic solvents (DESs) in sample preparation techniques.
Analytes Matrix IL/DES
Extraction
technique
Instrumental
analysis References
Resmethrin
Bifenthrin
Fenpropathrin
Cyhalothrin
Water samples 1-Vinyl-3-butylimidazolium
bis(trifluoromethylsulfonyl)-imide
MSPE GC–MS [96]
Ampicillin
Benzylpenicillin
Amoxicillin
Oxacillin
Cloxacillin
Milk samples [DABCO–C
3
OH]Cl or
1-(3-Hydroxypropyl)−1,4-
diazabicyclo[2.2.2]octan-1-ium chloride
MSPE UPLC–MS/MS [97]
Docosahexaenoic
Eicosapentaenoic
Arachidonic acid
Breast milk [SiO
2
-MIM-BF
4
] or SiO
2
-1-
Methylimidazolium tetrafluoroborate
SPE ELSD–HPLC [98]
Pioglitazone Drug samples 1-Hexyl-3-methyl-imidazolium-
hexafluorophosphate
DLLME HPLC–UV [99]
Fipronil
Metalaxyl Paclobutrazol
Myclobutanil
Napropamide
Thiacloprid Penconazole
Food samples Proline/propylene glycol (1 : 3) MSPE HPLC–UV [100]
Diflubenzuron
Triflumuron
Hexaflumuron
Flufenoxuron Chlorfluazuron
Tea and fruit
juices
Trihexyl tetradecyl phosphonium
chloride/tetradecyl alcohol
UA–
DLLME
HPLC–UV [101]
Oxytetracycline Doxycycline
Tetracycline
Water samples Choline chloride : ethylene glycol/
thymol : octanoic acid
DLLME HPLC–UV [102]
(Continued)
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Analytes Matrix IL/DES
Extraction
technique
Instrumental
analysis References
Salicylic acid
Oxaprozin
Diclofenac
Ibuprofen
Environmental
water and milk
samples
Guanidinium chloride and thymol UA–
DLLME
HPLC–UV [103]
Pesticides Tomato samples Choline chloride/ethylene glycol (1.25
mL) and choline chloride/n-butyric acid
(58 μL)
SBSE GC–MS [104]
Phthalate esters Soft drinks Thymol/octanoic acid VA–
DLLME
UHPLC–MS/
MS
[105]
Phthalic acid esters Tap and mineral
water
Menthol/acetic acid DLLME LC–UV [106]
Terpenes Spices Tetrabutylammonium bromide/
dodecanol
HS–
SDME
GC–MS [107]
Organophosphorus Water samples Benzyltriphenylphosphonim
bromide/1-undecanol
AA–
LPME
GC–MS [108]
Pb (II)
Cd (II)
Vegetables Citric acid/sucrose HI–DES–
ME
FAAS [109]
Ketoprofen
Diclofenac
Liver Menthol/formic acid EA–
DLLME
LC–MS/MS [110]
AA–LPME, atomic absorption liquid phase microextraction; Cd, cadmium; DLLME, dispersive liquid-liquid microextraction; EA–DLLME, effervescent-
assisted dispersive liquid-liquid microextraction; ELSD–HPLC, evaporative light scattering detection–high-performance liquid chromatography; FAAS, flame
atomic absorption spectrometry; GC–MS, gas chromatography mass spectrometry; HI–DES–ME, heat-induced deep eutectic solvent microextraction; HPLC–
UV, high-performance liquid chromatography ultraviolet detection; HS–SDME, headspace single-drop microextraction; LC–MS/MS, liquid chromatography
tandem mass spectrometry; LC–UV, liquid chromatography ultraviolet detection; MSPE, magnetic solid phase extraction; Pb, lead; SBSE, stir bar sorptive
extraction; SPE, solid phase extraction; UA–DLLME, ultrasound-assisted dispersive liquid-liquid microextraction; UHPLC–MS/MS, ultra-high performance
liquid chromatography–tandem mass spectrometry; UPLC–MS/MS, ultra-performance liquid chromatography–tandem mass spectrometry; VA–DLLME,
vortex-assisted liquid-liquid microextraction.
Table 3.5 (Continued)
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References 53
Deep eutectic solvents (DESs) were introduced originally in 2001 as a change from the
traditionally used organic solvents [94]. DESs could be considered a category of ILs, as they
share many characteristics and properties (low vapour pressure, non-flammability, non-
reactivity to water), but they cannot be considered true ILs as they are not totally composed
of ions. DESs are systems formed by a eutectic mixture of Lewis or Bransted acids and bases
that may contain a diffusion of anionic and/or cationic species. They are usually obtained
by complexing a quaternary ammonium salt with a metal salt or chemical bond donor [95].
In addition, the preparatory phase is considered more environmentally friendly than that of
ILs, and they are also easily biodegradable and recyclable, which makes them valid solvents
for use in sustainable analytical procedures. DESs are often divided into four categories:
DES types I, II, and IV are composed primarily of a metal salt (metal chloride hydrate) and
organic salts or other neutral compounds. DES type III consists primarily of an organic salt
as acceptor and hydrogen donor. Similar to DES are natural deep eutectic solvents (NADES),
which are formulated using natural elements generated by cellular metabolism (urea,
amino acids, sugars, choline, etc.). Several articles on analytical processes based on LLE and
SPE applying DES have been published and the most recent are summarised in Table 3.5.
3.4 Conclusion
The determination/quantification of compounds in complex matrices inevitably involves a
preparation phase whose primary objective is the isolation and concentration of analytes. This
preliminary phase also aims to obtain a clean sample appropriate for subsequent instrumental
analysis. Over the years, these preparation techniques have increasingly been oriented
towards simplification, automation, and the reduction of waste. Over time, several ecofriendly
methodologies have been introduced in the preparation step, including microextraction tech-
niques that use new and greener adsorbent materials or the use of alternative green solvents.
Sustainable development has now become the focus of every area, and this concept, extended
to analytical chemistry with the introduction of the principles of GAC, is continually growing.
In the near future, new extraction techniques are expected to be increasingly ecofriendly,
leading to laboratory procedures that have as little impact on the environment as possible.
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